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$1,325,000

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

4 Beds ⋅ 4 Baths ⋅ 100583485 MLS

Set on 3.21 private acres in Weymouth Heights, this 1924 estate offers architectural character, established gardens, and a detached guest cottage in one of Southern Pines' most treasured neighborhoods. Historic brick fencing lines portions of the drive, while mature pines, hardwoods, evergreens, and more than 300 flowering azaleas create a setting that has evolved beautifully over generations, just moments from downtown Southern Pines and Weymouth Woods. The 4-bedroom main residence blends thoughtful updates with original character, featuring hardwood floors, extensive mill work, custom built-ins, and four working fireplaces. Large windows frame views of the surrounding grounds, while multiple gathering spaces--including a spacious Great Room, dedicated office, and light-filled Carolina Room--provide flexibility for everyday living and entertaining. The kitchen is appointed with custom Rutt cherry cabinetry, Sub-Zero refrigeration, Dacor double ovens, a five-burner gas cook top, generous workspace, and abundant storage. The main-level primary suite offers a spacious bath, walk-in closet, fireplace, and direct connection to the Carolina Room and outdoor living spaces. Outside, flagstone walkways, stone terraces, expansive lawn areas, and a brick fireplace courtyard create inviting spaces to enjoy the property's exceptional landscape. A detached 659-square-foot guest cottage with a bedroom, full bath, living area, and fireplace provides additional flexibility for guests, extended family, or a private workspace. A rare opportunity to own a significant Weymouth Heights property with privacy, character, and convenience in the heart of Southern Pines.

285 N Bethesda Rd, Southern Pines

Listing courtesy of Everything Pines Partners LLC. Contact:

$749,000

A rare historic downtown Southern Pines home with genuine soul, thoughtful updates, and a story. A contributing structure within the National Register-listed Southern Pines Historic District, this circa-1915 home offers the rare combination of historic craftsmanship, thoughtful updates, generous storage, and walkable downtown living in the heart of Southern Pines. The National Register continuation sheet lists 360 S. Ashe St. as a contributing structure and specifically notes the screened porch, French doors, sash windows, rear additions, and central corbelled-cap chimney. Lovingly cared for and updated over the years as both a real home and an artist's studio, the home retains the warmth and craftsmanship that make older Southern Pines homes so special -- original hardwood floors, high ceilings, three fireplaces, French doors, built-ins, oversized windows, and architectural details that simply cannot be replicated in newer construction. This is not a neglected historic house waiting to be rescued; it is a soulful, livable home with original details still intact. For added buyer confidence, a professional pre-listing appraisal was completed on June 9, 2026 and valued the property at $781,000. The home's history adds another layer of charm. Local historians have connected the property to Dr. Ernest Poate, a physician, psychiatrist, and mystery novelist who wrote under the pen name Arthur Mallory -- a fitting 1930s chapter for a home in a town long loved by doctors, writers, artists, and creative professionals. That same creative spirit continues today in a house that has been home to an award-winning photographer for the past 20 years and has served as both a private residence and a place of inspiration. Inside, the home offers four spacious bedrooms, 2.5 bathrooms, and flexible living spaces with abundant built-in storage throughout. One of the most memorable features is the large banquette beside a dramatic wall of leaded-glass windows that open to the screened porch; an ideal spot for morning coffee, reading, casual dining, or gathering with friends. French doors connect the main living areas to the porch, while additional French doors from the primary suite open directly to the backyard, creating a graceful indoor-outdoor flow rarely found in historic downtown homes. The primary suite features a fireplace and large infinity tub, while the second main bath offers a classic clawfoot tub -- blending comfort, charm, and timeless Southern Pines style. Outside, the property reveals one of its most special features: a private and peaceful fenced backyard retreat in the middle of downtown. A picket-fenced front garden creates storybook curb appeal, while the backyard offers mature trees, garden space, and room to entertain, relax, or enjoy time with pets beneath the Carolina pines. As downtown living becomes increasingly dense, this property stands out for its sense of space - a setting that feels tucked away and serene while still being just a block from restaurants, coffee shops, Gulley's Garden Center, and downtown shops, with parks and the Sunrise Theater just a little farther beyond. A large basement provides valuable storage space not included in the heated square footage, adding practical flexibility that is especially rare in a historic home. More than just a house, this is a lovingly cared-for piece of Southern Pines history -- a warm, creative, and deeply livable home with original soul, thoughtful updates, rare outdoor space, and a story that belongs to the town itself.

4 Beds ⋅ 3 Baths ⋅ 100580757 MLS

A rare historic downtown Southern Pines home with genuine soul, thoughtful updates, and a story. A contributing structure within the National Register-listed Southern Pines Historic District, this circa-1915 home offers the rare combination of historic craftsmanship, thoughtful updates, generous storage, and walkable downtown living in the heart of Southern Pines. The National Register continuation sheet lists 360 S. Ashe St. as a contributing structure and specifically notes the screened porch, French doors, sash windows, rear additions, and central corbelled-cap chimney. Lovingly cared for and updated over the years as both a real home and an artist's studio, the home retains the warmth and craftsmanship that make older Southern Pines homes so special -- original hardwood floors, high ceilings, three fireplaces, French doors, built-ins, oversized windows, and architectural details that simply cannot be replicated in newer construction. This is not a neglected historic house waiting to be rescued; it is a soulful, livable home with original details still intact. For added buyer confidence, a professional pre-listing appraisal was completed on June 9, 2026 and valued the property at $781,000. The home's history adds another layer of charm. Local historians have connected the property to Dr. Ernest Poate, a physician, psychiatrist, and mystery novelist who wrote under the pen name Arthur Mallory -- a fitting 1930s chapter for a home in a town long loved by doctors, writers, artists, and creative professionals. That same creative spirit continues today in a house that has been home to an award-winning photographer for the past 20 years and has served as both a private residence and a place of inspiration. Inside, the home offers four spacious bedrooms, 2.5 bathrooms, and flexible living spaces with abundant built-in storage throughout. One of the most memorable features is the large banquette beside a dramatic wall of leaded-glass windows that open to the screened porch; an ideal spot for morning coffee, reading, casual dining, or gathering with friends. French doors connect the main living areas to the porch, while additional French doors from the primary suite open directly to the backyard, creating a graceful indoor-outdoor flow rarely found in historic downtown homes. The primary suite features a fireplace and large infinity tub, while the second main bath offers a classic clawfoot tub -- blending comfort, charm, and timeless Southern Pines style. Outside, the property reveals one of its most special features: a private and peaceful fenced backyard retreat in the middle of downtown. A picket-fenced front garden creates storybook curb appeal, while the backyard offers mature trees, garden space, and room to entertain, relax, or enjoy time with pets beneath the Carolina pines. As downtown living becomes increasingly dense, this property stands out for its sense of space - a setting that feels tucked away and serene while still being just a block from restaurants, coffee shops, Gulley's Garden Center, and downtown shops, with parks and the Sunrise Theater just a little farther beyond. A large basement provides valuable storage space not included in the heated square footage, adding practical flexibility that is especially rare in a historic home. More than just a house, this is a lovingly cared-for piece of Southern Pines history -- a warm, creative, and deeply livable home with original soul, thoughtful updates, rare outdoor space, and a story that belongs to the town itself.

360 S Ashe St, Southern Pines

Listing courtesy of NorthGroup. Contact:

$880,000

**NOW OFFERING A SELLER-PAID 2/1 RATE BUYDOWN** plus a **$2,500 lender credit** when financing through Rita Hairston with CrossCountry Mortgage, making this exceptional Downtown Southern Pines property even more affordable. 260 N Ridge Street is a well-maintained **1920 Dutch Colonial Revival**, thoughtfully expanded by Butler Constructs while preserving its original scale and character. The main floor flows naturally between a living room with a vented gas fireplace, separate dining room, spacious family room, and a cook's eat-in kitchen designed by ASID designer Denis McCullough, featuring eco-friendly countertops and Bosch appliances that remain with the home. A private main-floor office, newer mud/laundry room, and a full bath complete the 1,431-square-foot main level. Upstairs, four bedrooms, a bonus office nook, and a full bath offer peaceful, private space true to the home's 1920 character. A sketch is available illustrating the option to add a primary suite. Outside, a fully fenced patio and garden provide an exceptional, private space for entertaining, while the oversized detached garage offers flexibility as a workshop, gym, studio, or garage. The Town of Southern Pines has confirmed this corner lot can be split into **two additional buildable lots**--a rare, documented opportunity for a family compound, spec build, or income-producing investment in the heart of Downtown Southern Pines, just steps from shops and restaurants. Whether you are drawn to the character of the home, the private outdoor living, the confirmed development potential, or all three, this is a rare opportunity in Downtown Southern Pines. A recent home inspection is available, and all minor repairs have been completed.

4 Beds ⋅ 2 Baths ⋅ 100578609 MLS

**NOW OFFERING A SELLER-PAID 2/1 RATE BUYDOWN** plus a **$2,500 lender credit** when financing through Rita Hairston with CrossCountry Mortgage, making this exceptional Downtown Southern Pines property even more affordable. 260 N Ridge Street is a well-maintained **1920 Dutch Colonial Revival**, thoughtfully expanded by Butler Constructs while preserving its original scale and character. The main floor flows naturally between a living room with a vented gas fireplace, separate dining room, spacious family room, and a cook's eat-in kitchen designed by ASID designer Denis McCullough, featuring eco-friendly countertops and Bosch appliances that remain with the home. A private main-floor office, newer mud/laundry room, and a full bath complete the 1,431-square-foot main level. Upstairs, four bedrooms, a bonus office nook, and a full bath offer peaceful, private space true to the home's 1920 character. A sketch is available illustrating the option to add a primary suite. Outside, a fully fenced patio and garden provide an exceptional, private space for entertaining, while the oversized detached garage offers flexibility as a workshop, gym, studio, or garage. The Town of Southern Pines has confirmed this corner lot can be split into **two additional buildable lots**--a rare, documented opportunity for a family compound, spec build, or income-producing investment in the heart of Downtown Southern Pines, just steps from shops and restaurants. Whether you are drawn to the character of the home, the private outdoor living, the confirmed development potential, or all three, this is a rare opportunity in Downtown Southern Pines. A recent home inspection is available, and all minor repairs have been completed.

260 N Ridge St, Southern Pines

Listing courtesy of Everything Pines Partners LLC. Contact:

$390,000

$20,000 price improvement!!! Move in Ready, 3BR, 2 &1/2 bath neatly maintained Townhome in Hunters Ridge subdivision in Downtown Southern Pines! Enjoy an open-concept design, offering a perfect blend of comfort and style. The cathedral living room boasts soaring ceilings and a cozy gas fireplace, creating an inviting atmosphere for relaxing and entertaining. The custom kitchen is a chef's dream, equipped with a large prep island and breakfast bar, stainless steel appliances, and beautiful granite countertops. Hardwood floors adorn the foyer, living room, kitchen, and half bath on the main level, adding warmth and elegance to all the common living spaces. Enjoy tiled showers and baths throughout, complemented by an efficient tankless water heater for endless hot water. The walk-in attic provides ample storage space, while a separate loft or media room offers versatile living options. The main level master suite features a spacious walk-in closet, double sinks, a tiled shower, and a garden tub--perfect for unwinding after a busy day. The fenced rear yard provides privacy and a safe space for outdoor activities. Enjoy grilling and dawning on exterior concrete patio. Large one vehicle garage fitslarger trucks and works beautifully for a gym. There's also an additional parking space around the corner from the town home. Don't miss this very spacious town home with plenty of room for all your storage and privacy for entertaining. Located with easy access to Fort Bragg via Connecticut Avenue, this home is within walking distance to downtown shops, parks, and restaurants. Comfortable, convenient, and stylish--this townhome is ready to welcome you home!

3 Beds ⋅ 3 Baths ⋅ 100577086 MLS

$20,000 price improvement!!! Move in Ready, 3BR, 2 &1/2 bath neatly maintained Townhome in Hunters Ridge subdivision in Downtown Southern Pines! Enjoy an open-concept design, offering a perfect blend of comfort and style. The cathedral living room boasts soaring ceilings and a cozy gas fireplace, creating an inviting atmosphere for relaxing and entertaining. The custom kitchen is a chef's dream, equipped with a large prep island and breakfast bar, stainless steel appliances, and beautiful granite countertops. Hardwood floors adorn the foyer, living room, kitchen, and half bath on the main level, adding warmth and elegance to all the common living spaces. Enjoy tiled showers and baths throughout, complemented by an efficient tankless water heater for endless hot water. The walk-in attic provides ample storage space, while a separate loft or media room offers versatile living options. The main level master suite features a spacious walk-in closet, double sinks, a tiled shower, and a garden tub--perfect for unwinding after a busy day. The fenced rear yard provides privacy and a safe space for outdoor activities. Enjoy grilling and dawning on exterior concrete patio. Large one vehicle garage fitslarger trucks and works beautifully for a gym. There's also an additional parking space around the corner from the town home. Don't miss this very spacious town home with plenty of room for all your storage and privacy for entertaining. Located with easy access to Fort Bragg via Connecticut Avenue, this home is within walking distance to downtown shops, parks, and restaurants. Comfortable, convenient, and stylish--this townhome is ready to welcome you home!

195 Pinebranch Ct, Southern Pines

Listing courtesy of Sandhill Realty/Aberdeen. Contact:

$515,000

*15,000 Seller concession + Fridge and Blinds** Discover the Townhomes on Bennett. Conveniently located in the heart of downtown Southern Pines with its beautiful upscale brick exterior and a 2-car garage. Stepping inside the first floor, you'll find a bedroom, full en-suite bathroom, drop zone, and entry to your garage. Moving to the second floor of the home you can enjoy an open concept living room, kitchen, and dining area. The living room includes upgraded features such as a trey ceiling. The deluxe kitchen includes wall oven, electric cooktop, beautiful quartz countertops and a natural stone backsplash. Off the kitchen is a beautiful covered balcony that is perfect for relaxing or entertaining. Other second floor features include a pantry, coat closet, and half bathroom. As you move to the third floor of this townhome you will find the remaining two bedrooms. The primary bedroom and the second guest bedroom. The second guest bedroom serves as a dual primary suite with an en-suite bathroom. As you move down the hall, you will encounter the laundry room. Finally arriving in the primary suite with a large walk-in closet and primary bathroom. The upscale bathroom is complete with a frameless walk-in shower, and dual vanity sinks. This home has upscale finishes and LVP throughout, Come see all that Townhomes on Bennet has to offer!

3 Beds ⋅ 4 Baths ⋅ 100571616 MLS

*15,000 Seller concession + Fridge and Blinds** Discover the Townhomes on Bennett. Conveniently located in the heart of downtown Southern Pines with its beautiful upscale brick exterior and a 2-car garage. Stepping inside the first floor, you'll find a bedroom, full en-suite bathroom, drop zone, and entry to your garage. Moving to the second floor of the home you can enjoy an open concept living room, kitchen, and dining area. The living room includes upgraded features such as a trey ceiling. The deluxe kitchen includes wall oven, electric cooktop, beautiful quartz countertops and a natural stone backsplash. Off the kitchen is a beautiful covered balcony that is perfect for relaxing or entertaining. Other second floor features include a pantry, coat closet, and half bathroom. As you move to the third floor of this townhome you will find the remaining two bedrooms. The primary bedroom and the second guest bedroom. The second guest bedroom serves as a dual primary suite with an en-suite bathroom. As you move down the hall, you will encounter the laundry room. Finally arriving in the primary suite with a large walk-in closet and primary bathroom. The upscale bathroom is complete with a frameless walk-in shower, and dual vanity sinks. This home has upscale finishes and LVP throughout, Come see all that Townhomes on Bennet has to offer!

104 Lexington Ln, Southern Pines

Listing courtesy of Ascot Realty Inc.. Contact:

$600,000

Welcome Home to 332 Magnolia Circle with its Southern charm and rocking chair front porch! This home is spacious and light-filled and gives an aura of happiness as soon as you walk in the front door. Gleaming hardwood floors, walls of windows with custom-made shutters, and golf course views are just a few special things. The Kitchen has Stainless appliances, gorgeous green granite counters, and a double pantry as well as a Breakfast Nook in the Bay window. Off the Kitchen is a Laundry Room complete with a utility sink. A split bedroom plan boasts a serene and spacious Ensuite Master Bedroom and Bath on one side, and two guest bedrooms and bath on the other side. The third bedroom doesn't have a closet and has been used as flex/office space. The Master Bedroom is huge and has windows on two sides as well as a door onto the deck. There's a large walk-in master closet which opens into the bedroom and also the bathroom. The Bathroom has a jetted tub, beautiful tiled shower, large vanity with double sinks, and a linen closet. Outdoors, you can relax and watch golf from your screened porch, or your deck -- your choice! The 2 car garage has double doors, is a good size, and has pull down stairs to the attic. Charmingly, there is a lovely covered walk-way from the house to the side garage door. 332 Magnolia Circle has been well loved and beautifully maintained; it offers a whole house generator. Come for a visit and see how special this home is and all it has to offer!!

3 Beds ⋅ 2 Baths ⋅ 100562973 MLS

Welcome Home to 332 Magnolia Circle with its Southern charm and rocking chair front porch! This home is spacious and light-filled and gives an aura of happiness as soon as you walk in the front door. Gleaming hardwood floors, walls of windows with custom-made shutters, and golf course views are just a few special things. The Kitchen has Stainless appliances, gorgeous green granite counters, and a double pantry as well as a Breakfast Nook in the Bay window. Off the Kitchen is a Laundry Room complete with a utility sink. A split bedroom plan boasts a serene and spacious Ensuite Master Bedroom and Bath on one side, and two guest bedrooms and bath on the other side. The third bedroom doesn't have a closet and has been used as flex/office space. The Master Bedroom is huge and has windows on two sides as well as a door onto the deck. There's a large walk-in master closet which opens into the bedroom and also the bathroom. The Bathroom has a jetted tub, beautiful tiled shower, large vanity with double sinks, and a linen closet. Outdoors, you can relax and watch golf from your screened porch, or your deck -- your choice! The 2 car garage has double doors, is a good size, and has pull down stairs to the attic. Charmingly, there is a lovely covered walk-way from the house to the side garage door. 332 Magnolia Circle has been well loved and beautifully maintained; it offers a whole house generator. Come for a visit and see how special this home is and all it has to offer!!

332 Magnolia Cir, Southern Pines

Listing courtesy of Everything Pines Partners LLC. Contact:

$789,999

$15,000 BUILDER INCENTIVE!!!! Introducing the ''Emma'' floor plan offering 3 bedrooms, 3.5 baths, and approximately 2,629 square feet This modern design showcases clean architectural lines, elevated finishes, and thoughtfully planned living spaces throughout. The main level features an open layout anchored by a dramatic two-story dining room and a spacious great room with a gas fireplace. The kitchen is designed for both everyday living and entertaining, complete with a gas cooktop, wall microwave/oven combo, vented hood, and a wine fridge built into the island. Accordion doors off the main living area open to the covered deck, creating a seamless indoor-outdoor flow. The primary suite is located on the first floor and offers a spa-inspired bath with a freestanding tub, full tile shower, floating vanity, and a generous walk-in closet A mudroom, laundry room, powder room, and additional storage add convenience and functionality. Upstairs, you'll find two additional bedrooms, each with its own private bath, along with a versatile loft space. Accordion doors on the second level open to a covered balcony, extending the living area outdoors. A cable rail banister enhances the open feel and provides a sleek architectural detail overlooking the dining area below. Additional features include a tankless water heater and thoughtfully integrated storage throughout Don't miss this rare opportunity to own a modern, design-forward home in the heart of Southern Pines. . Ask about our Preferred Lender Incentive!

4 Beds ⋅ 4 Baths ⋅ 100556307 MLS

$15,000 BUILDER INCENTIVE!!!! Introducing the ''Emma'' floor plan offering 3 bedrooms, 3.5 baths, and approximately 2,629 square feet This modern design showcases clean architectural lines, elevated finishes, and thoughtfully planned living spaces throughout. The main level features an open layout anchored by a dramatic two-story dining room and a spacious great room with a gas fireplace. The kitchen is designed for both everyday living and entertaining, complete with a gas cooktop, wall microwave/oven combo, vented hood, and a wine fridge built into the island. Accordion doors off the main living area open to the covered deck, creating a seamless indoor-outdoor flow. The primary suite is located on the first floor and offers a spa-inspired bath with a freestanding tub, full tile shower, floating vanity, and a generous walk-in closet A mudroom, laundry room, powder room, and additional storage add convenience and functionality. Upstairs, you'll find two additional bedrooms, each with its own private bath, along with a versatile loft space. Accordion doors on the second level open to a covered balcony, extending the living area outdoors. A cable rail banister enhances the open feel and provides a sleek architectural detail overlooking the dining area below. Additional features include a tankless water heater and thoughtfully integrated storage throughout Don't miss this rare opportunity to own a modern, design-forward home in the heart of Southern Pines. . Ask about our Preferred Lender Incentive!

750 N Ashe St, Southern Pines

Listing courtesy of Carolina Summit Group, LLC. Contact:

$523,000

New construction Druther Homes in downtown Southern Pines -- with a rare full bath on the main level! Located at 261 N Hale Street, this 4-bedroom, 3-bath Craftsman-style home offers 1,953 square feet of efficient, thoughtfully designed living space just blocks from restaurants, coffee shops, shopping, and local parks. Enjoy true walkability in one of Southern Pines downtown neighborhoods, with quick access to Highway 1 for an easy commute to Fort Bragg, Raleigh, and surrounding areas. Designed for modern living, the open-concept layout centers around a spacious kitchen featuring built-ins, a large island, ample counter space, and a dedicated coffee bar -- perfect for busy mornings or entertaining friends. The full bathroom on the main level adds flexibility for guests, a home office, or multi-generational living. Upstairs, the primary suite provides a relaxing retreat complete with a soaking tub and well-appointed finishes. Two additional bedrooms offer space for work-from-home needs, family living, or visiting guests. Set on a .12-acre lot with a concrete driveway, this move-in-ready home blends Craftsman charm with smart design and low-maintenance living. Downtown Southern Pines living is calling to you!

4 Beds ⋅ 3 Baths ⋅ 100555495 MLS

New construction Druther Homes in downtown Southern Pines -- with a rare full bath on the main level! Located at 261 N Hale Street, this 4-bedroom, 3-bath Craftsman-style home offers 1,953 square feet of efficient, thoughtfully designed living space just blocks from restaurants, coffee shops, shopping, and local parks. Enjoy true walkability in one of Southern Pines downtown neighborhoods, with quick access to Highway 1 for an easy commute to Fort Bragg, Raleigh, and surrounding areas. Designed for modern living, the open-concept layout centers around a spacious kitchen featuring built-ins, a large island, ample counter space, and a dedicated coffee bar -- perfect for busy mornings or entertaining friends. The full bathroom on the main level adds flexibility for guests, a home office, or multi-generational living. Upstairs, the primary suite provides a relaxing retreat complete with a soaking tub and well-appointed finishes. Two additional bedrooms offer space for work-from-home needs, family living, or visiting guests. Set on a .12-acre lot with a concrete driveway, this move-in-ready home blends Craftsman charm with smart design and low-maintenance living. Downtown Southern Pines living is calling to you!

261 N Hale St, Southern Pines

Listing courtesy of eXp Realty. Contact: